The Oprah Winfrey Show aired its first episode 30 years ago today and went on to 25 seasons of ratings dominance. By the time it came to an end, in May 2011, the undisputed Queen of Daytime TV had interviewed thousands of people. Among the show’s countless memorable moments are several celeb appearances that stick with us either because of the revelations that were shared or the pure emotion that was evoked. Here’s a look back at 10 of our favorites.
- Mary Tyler Moore
Let’s start with the woman who managed to make Oprah Winfrey ugly cry. In 2002, Oprah did a show about her favorite celebrity women and, of course, Mary Tyler Moore was at the top of her list. The talk show personality had idolized both real-life Mary and the TV newswoman character she played on her eponymous show. As part of the episode, Oprah played back video of one of the “favorite, most fun things” she had ever done for her show: A recreation of the iconic Mary Tyler Moore Show opening, which ended with Oprah making that famous hat toss. “Whenever I’m having a down day, I just pop that thing in. I love that!” she giggled.
The piece also included an older clip of when Mary Tyler Moore surprised Oprah by calling into the show. Little did Oprah know that during that 2002 show Mary was about to walk onstage and embrace her in person.
2. Whitney Houston
When Oprah sat down with Whitney Houston in 2009 for her first interview in about seven years, the singer had been divorced from R&B star Bobby Brown for two years. Their 14-year marriage had been tumultuous at best and beyond the bats***-craziness of their reality show, Being Bobby Brown. This interview with Oprah gave a lot of insight into the mind and life of the beloved singer.
A calm and composed Whitney went into detail about the dysfunctional — yet loving — relationship she and Bobby had. She also disclosed the depths of her drug use, though the ABC interview she would do a few years later was the one that brought about the phrase “Crack is wack.” She insisted she was drug-free but admitted she still had desires. “I can only think one day at a time,” she said.
In one particularly heartbreaking section of the one-on-one, Whitney spoke about her daughter, Bobbi Kristina, and noted she was concerned about the behavior between her parents that she may have witnessed. That’s why she decided to move away with her to California for a short time.
“It was enough. She saw enough. The spitting in the face was enough. She said: ‘Mom, did he spit in your face?’ And I looked in her eyes and she looked in mine and I said: ‘Yes. But it’s all right.’ And she said: ‘No, it’s not. No, it’s not. It’s not, Mom. It’s not all right,‘” Whitney recalled. “I said: ‘If you can do me a favor. Just do this for Mommy. I’m going to put my trust in God. You put your trust in me. You may not understand it now, but just trust me. I’m not letting you go. I will hold on to you with my dear life. Just trust me. And we will get up out of this. And we’ll be happier for it. And then as you get older, I’ll tell you little by little as to why things are happening and why Mommy has to go.”
3. Tyler Perry
Tyler Perry, who built an empire on his Madea movie franchise, held nothing back as he tearfully spoke to Oprah in 2010 about his tragic upbringing. Describing his childhood as “a living hell,” the actor/writer/director/producer opened up about the father who abused him and the later sexual molestation he suffered at the hands of three men, as well as the mother of one of his friends.
“I think that everyone who’s been abused, there is a string to the puppet master, and they’re holding you hostage to your behaviors and what you do,” he said of his decision to speak out and try to help others who had been abused. “At some point, you have to be responsible for them. What I started to do is untie the strings and chase them down to where they came from. And I was able to free myself and understand that even though these things happened to me, it was not me.”
4. Mackenzie Phillips
Mackenzie Phillips, best known for her role as Julie on One Day at a Time, shocked the world in 2009 when she opened up to Oprah about a revelation in her memoir High on Arrival. She shared the secret she had hid for years: that she had an incestuous relationship with her father, the Mamas and the Papas band member John Phillips. She recalled that in the midst of at least one drug-fueled haze she woke up from a blackout to find herself having sex with her dad. Their sexual relationship ended after she got pregnant and didn’t know who the father was. Her dad, John, who was potentially the father of her unborn child, paid for the abortion.
Given the frenzy around her announcement and the response from her family, Mackenzie later told Oprah that she had some regrets about how she decided to relay her story. “It was sort of like a runaway train that I had no power of stopping,” she explained. “Maybe I would have gotten [my family members] all together and prepared them better. They already knew … you see, the thing is when they all say, ‘We didn’t know,’ they all already knew and so that is something that one just had to deal with.”
5. Kirstie Alley
Having famously battled with weight issues for years, Cheers star — and then Jenny Craig spokesperson — Kirstie Alley surprised everyone when she strutted out onto Oprah’s stage in 2006 wearing a bikini to show off her 75-pound weight loss. While it was an iconic moment, she eventually put the weight back on, and in 2009 confessed to Oprah that she was humiliated to still be talking about her weight. “The most painful thing for me is that I have all these people that I inspired and then I let them down.”
In 2014, Kirstie teamed up with Jenny Craig again and has had major success with the program. You go, girl!
6. Michael Jackson
Only the incomparable Oprah Winfrey could score an interview with the notoriously private King of Pop. In 1993, Michael Jackson welcomed Oprah and her viewers onto his Neverland Ranch, where the two discussed everything from what was the deal with his hyperbaric chamber to whether or not he was a virgin. It was both a revelation and a curiosity for the millions of adoring fans watching. They toured the grounds and he even busted a few moves, including the Moonwalk, for Oprah. And to add to the spectacle, Michael’s good friend, the aging but still beautiful Elizabeth Taylor made a brief appearance. She was on hand to support Michael and ended up extolling his many virtues when asked what she wanted the world to know about her friend. “What a wonderful, giving, caring man he is. And how good he is too,” she said. “And he’s wildly funny.”
7. Donny and Marie Osmond
As Oprah announced early on, this 2007 interview with Donny and Marie Osmond was “history in the making” since the studio was “filled with over 100 of the world famous Osmonds.” It was to commemorate the 50th anniversary of the talented Osmond family and was taped after the passing of patriarch George. While most of the world came to know brother and sister Donny and Marie in the ’70s because of their hit variety show, George and Olive Osmond had a total of nine children, 55 grandchildren, and 48 great grandkids.
Marie also gifted Oprah with a one-of-a-kind porcelain doll meant to resemble Oprah as a child as a thank-you for bringing her large family together on her show. “This is a rare moment. We won’t always have everybody. There will be a few that have to work or whatever,” said Marie. “And this kind of an opportunity is a once-in-a-lifetime.”
8. Tom Cruise
Who could forget the 2005 interview Oprah did with Tom Cruise? As the actor pumped his fists in the air, laughed maniacally, and jumped all over the place — including on her couch — Oprah had to say, “Something happened to you … We’ve never seen you behave this way before!” Indeed, the international box-office star was far from his normal composed self. He was in love.
At the time, Katie Holmes was just 26 and the object of Tom’s affection. As the crowd chanted her name, Tom went backstage to get her and proudly showed her off to Oprah and her audience. And so began the Katie and Tom era that would impact public perception of Tom and end in divorce in 2012.
9. Iyanla Vanzant
When Oprah introduced her audience to the already popular author, speaker, and spiritual coach Iyanla Vanzant in 1998, she became an instant hit with her simple message: “To live better, you’ve got to love yourself.” She had been a teen mother and rape survivor who’d also been on welfare until she was able to put herself through law school and create her self-help empire. But her budding relationship with Oprah ended abruptly in 2000 for reasons unknown … until this 2011 reunion episode.
The two women cleared the air on a miscommunication about whether or not Iyanla had made an ultimatum in pushing for her own show from Oprah (as fellow standout guest speaker Dr. Phil had achieved), with Iyanla saying she never intended to give Oprah an ultimatum and regretted their misunderstanding. In the ensuing years, she had landed a show with Barbara Walters’s production company but that fell apart, as did her finances and marriage. Thankfully, all was forgiven on Oprah’s end, and Iyanla found herself firmly back in the fold with her Iyanla, Fix My Life series on OWN.
10. Sarah Ferguson
The Duchess of York made a beeline for Oprah when she became embroiled in a scandal in 2010. She’d been caught on tape trying to arrange a $750,000 payment for exploiting her connection to her ex-husband Prince Andrew and getting others access to him. As the British tabloids took her to task, Fergie pleaded her case to Oprah, basically saying she had a drinking problem and that is what caused her bad judgment. “I was in the gutter at that moment,” she confessed. “I’d been drinking. I was not in my right place.”
Fergie eventually smoothed things over with Prince Andrew and even came to his defense when he was in the midst of his own scandal a few years ago.
Happy anniversary, Oprah!